[ CAS No. 144-83-2 ] {[proInfo.proName]}

Name: 144-83-2|4-Amino-N-(pyridin-2-yl)benzenesulfonamide|98+%
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Quality Control of [ 144-83-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 144-83-2 ]

Product Details of [ 144-83-2 ]

CAS No. :	144-83-2	MDL No. :	MFCD00038036
Formula :	C₁₁H₁₁N₃O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GECHUMIMRBOMGK-UHFFFAOYSA-N
M.W :	249.29	Pubchem ID :	5336
Synonyms :	NSC 41791;NSC 4753;Pyriamid;Plurazol;A 499;Sulphapyridine	Chemical Name :	4-Amino-N-(pyridin-2-yl)benzenesulfonamide

Calculated chemistry of [ 144-83-2 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	65.76
TPSA :	93.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.82 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.76
Log Po/w (XLOGP3) :	0.0
Log Po/w (WLOGP) :	2.36
Log Po/w (MLOGP) :	0.1
Log Po/w (SILICOS-IT) :	0.25
Consensus Log Po/w :	0.69

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.71
Solubility :	4.86 mg/ml ; 0.0195 mol/l
Class :	Very soluble
Log S (Ali) :	-1.51
Solubility :	7.64 mg/ml ; 0.0306 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-4.17
Solubility :	0.017 mg/ml ; 0.0000684 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.56

Safety of [ 144-83-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 144-83-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 144-83-2 ]
Downstream synthetic route of [ 144-83-2 ]

[ 144-83-2 ] Synthesis Path-Upstream 1~2

1
[ 144-83-2 ]
[ 69-72-7 ]
[ 599-79-1 ]

Yield	Reaction Conditions	Operation in experiment
95.4%	Stage #1: With hydrogenchloride; sodium nitrite In water at 2℃; for 0.333333 h; Stage #2: With sodium hydroxide In water at 7℃; for 1.5 h;	Example 4 Place sulfapyridine and 4 (amount of substance) hydrochloric acid (amount of substance of sulfapyridine is for 1) in a reaction flask. Stir until dissolve. Adjust temperature to 2°C then start dropping 1.10sodium nitrite ( amount of substance of sulfapyridine is 1m).Allocate aqueous solution. React for 20min to obtain a solution containingdiazonium salt intermediate. Name this to be A. Place 1.3 salicylic acid and part of sodium hydroxide ( amount ofsubstance of sulfapyridine is 1m ) in a reaction flask. After adjustingtemperature to 7°C,slowly start dropping the above-mentioned A to the above-mentioned reactionflask. At the same time, drop the remaining sodium hydroxide solution to controlthe pH of the reaction liquid to 10. Start reaction. The used amount of sodiumhydroxide is 4 (amount ofsubstance of sulfapyridine is 1m ). React for 1.5h. Stop reaction. Add THF tothe reaction mixture. Add hydrochloric acid to adjust pH to 3. Heat underreflux for a period of time. Cool to 30°C to crystallize. Filter out crystals to obtain crudesulfasalazine. Place 10g crude sulfasalazine,70g dimethyl sulfoxide, 30g water in 250mL flask. Also, add solid sodiumhydroxide to mixture with pH of 9. Heat the mixture in the flask to 80^oCto fully dissolve. After dissolving, add hydrochloric acid, dropwise, to adjustthe pH of the solution to 1. Incubate at 80°Cfor 2h then cool to 0°C then filter to obtain crude crystals. Add crystalsto water. Add solid sodium hydroxide. Heat to 80°C. Dissolve to obtain solutionwith pH 9. Sequentially, undergo, at 70°C, decolorization using 7g activatedcharcoal and filtration. Add, dropwise, hydrochloric acid to crystals with pH1.Dry crystals to obtain pure sulfasalazine. In this case, 9.54g ofpure sulfasalazineare collected. Yield is 95.4percent. HLPC purity test shows 99.7percent.

Reference： [1] Patent: CN105348184, 2016, A, . Location in patent: Paragraph 0049; 0050; 0051; 0052; 0053
[2] Patent: CN105330599, 2016, A, . Location in patent: Paragraph 0045; 0046
[3] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 1987 - 2004

2
[ 144-83-2 ]
[ 2835-95-2 ]
[ 1395084-25-9 ]

Yield	Reaction Conditions	Operation in experiment
14%	Stage #1: With hydrogenchloride In methanol; water; acetonitrile at -2 - 0℃; for 0.0833333 h; Stage #2: With isopentyl nitrite In methanol; water; acetonitrile at 0℃; for 0.166667 h; Inert atmosphere Stage #3: With potassium carbonate In methanol; water; acetonitrile at 0 - 5℃; for 1.25 h; Inert atmosphere	B. Synthesis ofTarget-7: MS0129436To a stirred solution of amine (12 g, 0.048 lmol) in methanol and ACN (1 : 1, 240 mL) was added cone. HC1 (20.4 mL) and stirred at 0 °C to -2 °C for 5 min. Then isoamyl nitrite (6.48mL, 0.553 mol) was added dropwise for 10 min under inert atmosphere and the reaction mixture was stirred at 0°C for 45 min. Meanwhile homogenous solution of 5- aminocresol (5.92 g, 0.0481 mol) and potassium carbonate (33.2 g, 0.24067 mol) in water (500 mL) was prepared. This solution was de-gassed by purging N₂ for 15 min and then was added via cannula to the previously prepared diazonium salt solution at 0-5°C and the resulting reaction mixture was stirred at 0-5°C for 1 h. The reaction mixture was then acidified with 1 N HC1 (pH = 6) and the reaction was filtered. Fitrate was extracted with EtOAc (2 x 300mL) and the solid ppt was stirred in isopropyl alcohol for 3 h at room temperature and filtered. The combined organic extracts were distilled under reduced pressure to obtain orange-red crude residue. The solid was purified by columnchromatography (twice) using methanol/DCM to afford target 7 (2.6g, 14percent yield).TLC: 5percent MeOH/DCM, Rf: 0.5)HPLC purity: 98.63percent, IP 10041325Melting point: 217.2°CMass: 383 (M+l) ¹HNMR (500MHz, DMSOd6) 5:9.22 (bs, 1H), 8.0(m, 3H), 7.9(d, 2H), 7.72(t, 1H), 7.54 (s, 2H), 7.2 (d, 1H), 6.8 (t, 1H), 2.21 (s, 6H).

Reference： [1] Patent: WO2012/116170, 2012, A1, . Location in patent: Page/Page column 68-69
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 22, p. 9251 - 9264

[ 144-83-2 ] Synthesis Path-Downstream 1~26

1
[ 1749-68-4 ]
[ 144-83-2 ]
N-(6-amino-2-methyl-pyrimidin-4-yl)-sulfanilic acid-[2]pyridylamide; hydrochloride [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 106

2
[ 7469-77-4 ]
[ 144-83-2 ]
4-(4-hydroxy-3-methyl-[1]naphthylazo)-benzenesulfonic acid-[2]pyridylamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1945,vol. 67,p. 811

3
[ 2246-44-8 ]
[ 144-83-2 ]
4-(4-amino-3-methyl-[1]naphthylazo)-benzenesulfonic acid-[2]pyridylamide [ No CAS ]

Reference： [1]Svensk Kemisk Tidskrift,1942,vol. 54,p. 223,230

4
[ 83-40-9 ]
[ 144-83-2 ]
2-hydroxy-3-methyl-5-(4-[2]pyridylsulfamoyl-phenylazo)-benzoic acid [ No CAS ]

Reference： [1]Patent: US2396145,1942,

5
[ 870-72-4 ]
[ 144-83-2 ]
(4-[2]pyridylsulfamoyl-anilino)-methanesulfonic acid [ No CAS ]

Reference： [1]Patent: US2305260,1939,

6
[ 144-83-2 ]
[ 131700-65-7 ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium azide; tert.-butylnitrite In tetrahydrofuran; water at 40℃; for 0.5h; Microwave irradiation;	General procedure General procedure: Sodium azide (78 mg, 1.20 mmol, 3 equiv.) wasintroduced in a microwave flask equipped with a stirringbar and solubilized with water (150 µL). To this solution,the remaining reagents were added in the following order: solvent reaction (1 mL), 4-aminobenzenesulfonamide (16-22) (0.4 mmol, 1 equiv.) and tert-butyl nitrite(t-BuONO). The mixture was stirred and heated undermicrowave radiation at 150 W. The reaction was followedby TLC and after completion, the reaction mixture waspartitioned between hexane and EtOAc. The aqueousphase was extracted with EtOAc (3 times), and the organicphase was dried over Na2SO4, filtered and concentrated.The product was obtained after flash chromatographyon a Biotage Horizon, using 12 mm flash cartridge,flow 8 mL min-1; hexane/EtOAc; gradient 0-40% and40%-40% (v/v).
40%	Stage #1: sulphapyridine With sulfuric acid In water at 0℃; Stage #2: With sodium nitrite In water at 0 - 20℃; for 0.166667h; Stage #3: With sodium azide; urea In water at 20℃;	4.2.1. Synthesis of azide-benzenesulfonamides 8-14 General procedure: Each 4-aminobenzenesulfonamide (3.0 mmol) was added in asolution of concentrated sulfuric acid (0.5 mL) and H2O (3.0 mL)and then cooled to 0 C in an ice bath. A solution of NaNO2 (3.0mmol) in water (2.1 mL) was added dropwise to the reaction andleft stirring for 10 min. After a color change to a yellowish toneand appearance of foam in the medium, solid urea (150 mg) wasadded followed by NaN3 solution (9.0 mmol, 1.5 eq) in H2O (3.2mL) dropwise. Finally, after stirring for few minutes each reactionwas filtered through Buchner funnel and washed subsequentlywith 5% NaHCO3 and H2O. Each obtained product was dried underreduced pressure and analyzed by TLC, being verified at increasedretention factors (Rf) if compared to the corresponding startingmaterials. Compounds 8-14 were obtained in corresponding yieldsof 38% (8), 45% (9), 91% (10), 52% (11), 42,5% (12), 40% (13) and 76%(14). 1H NMR and IR [2100 cm1 (N3)] (2100 cm1) analysis of 8-14 were in accordance with the literature.28
	With sulfuric acid; sodium nitrite anschliessend mit Kaliumacetat und N₂H₄;

Stage #1: sulphapyridine With hydrogenchloride; sodium nitrite In water Stage #2: With sodium azide In water

Reference： [1]Junqueira, Getúlio G.; Carvalho, Marcelo R.; De Andrade, Peterson; Lopes, Carla D.; Carneiro, Zumira A.; Sesti-Costa, Renata; Silva, João S.; Carvalho, Ivone [Journal of the Brazilian Chemical Society, 2014, vol. 25, # 10, p. 1872 - 1884]
[2]Marchiori, Marcelo Fiori; Riul, Thalita B.; Oliveira Bortot, Leandro; Andrade, Peterson; Junqueira, Getúlio G.; Foca, Giuseppina; Doti, Nunzianna; Ruvo, Menotti; Dias-Baruffi, Marcelo; Carvalho, Ivone; Campo, Vanessa Leiria [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 21, p. 6049 - 6059]
[3]Current Patent Assignee: PFIZER INC - US2254191, 1940, A
[4]Rezki, Nadjet; Almehmadi, Meshal A.; Ihmaid, Saleh; Shehata, Ahmed M.; Omar, Abdelsattar M.; Ahmed, Hany E.A.; Aouad, Mohamed Reda [Bioorganic Chemistry, 2020, vol. 103]

7
[ 1028-11-1 ]
[ 144-83-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With iron; ammonium chloride In methanol at 80℃; for 3h;	1.2 p-nitrobenzenesulfonamide pyridine is reduced to p-aminobenzenesulfonamide pyridine: A solution of p-nitrobenzenesulfonamide pyridine (1 mmol) in nano Fe powder (3 mmol), NH4Cl (5 mmol) and methanol solvent,The reaction was stirred at 80 ° C for 3 hours.After the reaction was cooled, the mixture was diluted with AcOEt, filtered, and the filtrate was steamed to precipitate the product.Add water in the precipitate, add sodium bicarbonate to maintain the aqueous solution was alkaline, and then cooled in an ice bath to precipitate a white solid,Filtration and drying gave p-aminobenzenesulfonamide pyridine in 81% yield.
	With iron; acetic acid
	With iron; ammonium chloride In methanol; water at 70℃; for 4h;

With sodium hydroxide; water; iron(II) sulfate

Reference： [1]Current Patent Assignee: SOUTH CHINA AGRICULTURAL UNIVERSITY - CN106316938, 2017, A Location in patent: Paragraph 0038; 0039; 0040; 0041; 0042
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - CH220046, 1940, A
[3]Zhang, Guangtao; Plotnikov, Alexander N.; Rusinova, Elena; Shen, Tong; Morohashi, Keita; Joshua, Jennifer; Zeng, Lei; Mujtaba, Shiraz; Ohlmeyer, Michael; Zhou, Ming-Ming [Journal of Medicinal Chemistry, 2013, vol. 56, # 22, p. 9251 - 9264]
[4]Current Patent Assignee: SANOFI - DE737796, 1938, C [DRP/DRBP Org.Chem.][DRP/DRBP Org.Chem.] Current Patent Assignee: SANOFI - US2275354, 1938, A

8
[ 144-83-2 ]
[ 871-58-9 ]
2-pyridyl sulphamidophenyl-O-butyl xanthate [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1980,vol. 57,p. 857 - 858

9
[ 72875-83-3 ]
[ 144-83-2 ]
4-(6-iodo-4-oxo-2-phenyl-4H-quinazolin-3-yl)-N-pyridin-2-yl-benzenesulfonamide [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1997,vol. 74,p. 619 - 623

10
[ 144-83-2 ]
[ 119-84-6 ]
2-hydroxy-5-[4-[[(2-pyridinyl)-amino]-sulfonyl]phenylazo]benzenepropanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; sodium nitrite In water; acetone	3 2-hydroxy-5-[4-[[(2-pyridinyl)-amino]-sulfonyl]phenylazo]benzenepropanoic acid EXAMPLE 3 2-hydroxy-5-[4-[[(2-pyridinyl)-amino]-sulfonyl]phenylazo]benzenepropanoic acid 25.0 g of sulfapyridine was dissolved in 80 ml of water and 24 ml of conc. hydrochloric acid. The solution was kept at 0° C. 7.0 g of sodium nitrite in 40 ml of cold water was added during about 10 min. with stirring and cooling by the addition of 100 g ice in portions. 14.8 g of 3,4-dihydro-(2H)-1-benzopyran-2-one (the lactone of 2-hydroxy-benzene-propanoic acid) was added to 16 g of sodium hydroxide in 200 ml of water. The mixture was heated to 80°-90° C. until all of the lactone had been hydrolyzed and dissolved. The solution was cooled to about 0° C. and the diazonium salt solution quickly added with stirring. After 5 min., the solution was acidified with dilute hydrochloric acid. An oily mass precipitated. After decantation of the aqueous phase and digestion with 200 ml of acetone, the product crystallized and was filtered off.

Reference： [1]Current Patent Assignee: PFIZER INC - US4628083, 1986, A

11
[ 10030-80-5 ]
[ 144-83-2 ]
C₁₇H₂₁N₃O₇S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With acetic acid In ethanol; water; N,N-dimethyl-formamide at 60℃; for 2h;

Reference： [1]Location in patent: experimental part Kamel, Mohsen M.; Ali, Hamed I.; Anwar, Manal M.; Mohamed, Neama A.; Soliman, AbdelMohsen M. [European Journal of Medicinal Chemistry, 2010, vol. 45, # 2, p. 572 - 580]

12
[ 144-83-2 ]
[ 29284-76-2 ]
[ 1204290-52-7 ]
[ 1204290-51-6 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water at 115℃; for 72h;

Reference： [1]Location in patent: experimental part Lawrence, Harshani R.; Kazi, Aslamuzzaman; Luo, Yunting; Kendig, Robert; Ge, Yiyu; Jain, Sanjula; Daniel, Kenyon; Santiago, Daniel; Guida, Wayne C.; Sebti, Said M. [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 15, p. 5576 - 5592]

13
[ 144-83-2 ]
[ 29284-76-2 ]
[ 1204290-54-9 ]
[ 1204290-53-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: sulphapyridine; 2,3-dichloro-6-nitronaphthalene-1,4-dione In ethanol; water at 115℃; for 72h; Stage #2: With palladium 10% on activated carbon; hydrogen In methanol; N,N-dimethyl-formamide at 20℃;

14
[ 84540-50-1 ]
[ 144-83-2 ]
[ 1395084-37-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: sulphapyridine With hydrogenchloride In methanol; water; acetonitrile at 0℃; for 0.25h; Stage #2: With isopentyl nitrite In methanol; water; acetonitrile at 0℃; for 0.916667h; Inert atmosphere; Stage #3: 2-chloro-6-methyl-1-hydroxy-3-aminobenzene With potassium carbonate In methanol; water; acetonitrile at 0℃; for 0.5h; Inert atmosphere;	3.C C. Synthesis of CM363Synthesis of (E)-4-((2-amino-3-chloro-4-hydroxy-5-methylphenyl) diazenyl)-N-(pyridin-2- yl)benzenesulfonamide.A 50 mL round bottom flask was charged with sulfapyridine (100.0 mg, 0.40 mmol, 1.0 eq.) and concentrated HCl (87.5 mg, 160 μ, 2.40 mmol, 5.98 eq.). The mixture was dissolved in a methanol/acetonitrile mixture (3 mL/3 mL). The solution was cooled to 0 °C and stirred for 15 min. Iso-amyl nitrite (47.0 mg, 54 μ^, 0.40 mmol, 1.0 eq.) was added drop by drop under argon over 10 min. The solution was stirred at 0 C for 45 min. Meanwhile, another 50 mL round bottom flask 3-amino-2-chloro-6-cresol (63.0 mg, 0.40 mmol, 1.0 eq.) and potassium carbonate (276.3 mg, 2.0 mmol, 5.0 eq.). To this mixture was added 1.0 mL methanol and 8.0 mL of DI H20. The solution was deoxygenated for 15 min. The resultant solution was cooled to 0 °C. The previously prepared amber color diazonium ion was added drop wise under argon over 15 min. At the end of the addition, the pH of the solution was maintained between 8-10. The solution was allowed to stir at 0 °C for 1 h and then quenched with 1 N HCl to reach pH 1. Massive precipitation was observed. The product was filtered and dried under vacuum. The pure product appeared as a fine red powder (167.0 mg, 99%). 1H NMR (DMSO) δ 1 1.51 (s, 1H), 8.04 (s, 1H), 7.97-7.78 (m, 3H), 7.78-7.62 (m, 3H), 7.53 (s, 1H), 7.15 (s, 1H), 6.89 (s, 1H), 6.73 (br s, 2H), 1.98 (s, 3H). MS calculated forCI8HI6C1N503S [M+H]+ 418.08, found 418.08. Purity >99%, tR = 5.5 min.
	Stage #1: sulphapyridine With hydrogenchloride In methanol; acetonitrile at 0℃; for 0.25h; Stage #2: With isopentyl nitrite In methanol; acetonitrile at 0 - 20℃; for 0.75h; Inert atmosphere; Stage #3: 2-chloro-6-methyl-1-hydroxy-3-aminobenzene With potassium carbonate In methanol; acetonitrile at 0 - 20℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI - WO2012/116170, 2012, A1 Location in patent: Page/Page column 69
[2]Zhang, Guangtao; Plotnikov, Alexander N.; Rusinova, Elena; Shen, Tong; Morohashi, Keita; Joshua, Jennifer; Zeng, Lei; Mujtaba, Shiraz; Ohlmeyer, Michael; Zhou, Ming-Ming [Journal of Medicinal Chemistry, 2013, vol. 56, # 22, p. 9251 - 9264]

15
[ 346-55-4 ]
[ 144-83-2 ]
[ 1489236-25-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	In N,N-dimethyl-formamide; for 12h;Reflux;	General procedure: A mixture of 1 (2.31 g, 0.01 mol) and the corresponding sulfadrugs (0.012 mol) in dry DMF (20 mL) was refluxed for 12 h. The solid obtained after concentration was filtered and crystallized from dioxane to give 2-14, respectively.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 69,p. 373 - 383

16
[ 13319-71-6 ]
[ 144-83-2 ]
(E)-4-((3-bromo-4-hydroxy-5-methylphenyl)diazenyl)-N-(pyridin-2-yl)benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9251 - 9264

17
[ 608-33-3 ]
[ 144-83-2 ]
(E)-4-((3,5-dibromo-4-hydroxyphenyl)diazenyl)-N-(pyridin-2-yl)benzenesulfonamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 9251 - 9264

18
[ 2198-53-0 ]
[ 144-83-2 ]
(E)-N-(2,6-dimethyl-4-((4-(N-(pyridin-2-yl)sulfamoyl)phenyl)diazenyl)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: sulphapyridine With hydrogenchloride In methanol; acetonitrile at 0℃; for 0.25h; Stage #2: With isopentyl nitrite In methanol; acetonitrile at 0 - 20℃; Inert atmosphere; Stage #3: N-(2,6-dimethylphenyl)acetamide With potassium carbonate In methanol; acetonitrile at 0 - 20℃; Inert atmosphere;

Reference： [1]Zhang, Guangtao; Plotnikov, Alexander N.; Rusinova, Elena; Shen, Tong; Morohashi, Keita; Joshua, Jennifer; Zeng, Lei; Mujtaba, Shiraz; Ohlmeyer, Michael; Zhou, Ming-Ming [Journal of Medicinal Chemistry, 2013, vol. 56, # 22, p. 9251 - 9264]

19
[ 144-83-2 ]
[ 85-87-0 ]
[ 1491132-81-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: sulphapyridine With hydrogenchloride In methanol; acetonitrile at 0℃; for 0.25h; Stage #2: With isopentyl nitrite In methanol; acetonitrile at 0 - 20℃; Inert atmosphere; Stage #3: pyridoxamine With potassium carbonate In methanol; acetonitrile at 0 - 20℃; Inert atmosphere;

20
[ 5784-45-2 ]
[ 144-83-2 ]
4-(phthalazin-1-ylamino)-N-(pyridin-2-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In ethanol for 24h; Reflux;	4 General procedure for the preparation of compounds (5a-f) General procedure: A mixture of 1-chlorophthalazine 3 (1g, 6mmol), the appropriate benzenesulfonamide (6mmol) and anhydrous potassium carbonate (12mmol) in ethanol (10ml) was heated under reflux for 24h. The mixture was poured onto ice-cooled water and neutralized with concentrated hydrochloric acid. The separated solid was filtered off and crystallized from the appropriate solvent. 4.1.1.4 4-(Phthalazin-1-ylamino)-N-(pyridin-2-yl)benzenesulfonamide (5d) M.p. 190-192 °C, yield: 75%. IR νmax cm-1: 3414 (NH), 3070 (aromatic CH), 1334, 1149 (SO2). 1H NMR (DMSO-d6): 300 MHz, δ = 6.53 (d, 2H, J = 8.5 Hz, J = 9 Hz, CH-2+CH-6 phenyl), 6.85 (t, 1H, J = 7.5 Hz, CH-3 pyridine), 7.05 (d, 1H, J = 7.8 Hz, CH-5 pyridine), 7.5 (d, 2H, J = 8.7 Hz, CH-3+CH-5 phenyl), 7.64 (t, 1H, J = 7.8 Hz, CH-4 pyridine), 7.81 (t, 1H, J = 7.8 Hz, CH-6 phthalazine), 7.90-8.15 (m, 2H, CH-7 phthalazine + CH-6 pyridine), 8.24 (d, 1H, J = 7.6 Hz, CH-5 phthalazine), 8.60 (d, 1H, J = 7.5 Hz, CH-8 phthalazine), 9.09 (s, 1H, CH-4 phthalazine), 10.04 (s, 2H, NH + SO2NH, exchanged by D2O). MS m/z: 377 [M+]. Anal. Calcd. for C19H15N5O2S (377.42): C, 60.47; H, 4.01; N, 18.56. Found: C, 60.54; H, 4.11; N, 18.82.

Reference： [1]Amin, Kamilia M.; Barsoum, Flora F.; Awadallah, Fadi M.; Mohamed, Nehal E. [European Journal of Medicinal Chemistry, 2016, vol. 123, p. 191 - 201]

21
[ 28900-10-9 ]
[ 144-83-2 ]
4-(3-cyano-6-methylpyridin-2-ylamino)-N-(pyridin-2-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine; In N,N-dimethyl-formamide; for 18h;Reflux;	General procedure: A mixture of <strong>[28900-10-9]2-chloro-6-methylnicotinonitrile</strong> (II)(1.52 g, 0.01 mol) and corresponding sulfonamide derivatives (0.012 mol) in dry dimethylformamide(10 mL) containing 3 drops of trimethylamine was refluxed for 18 h then left to cool. The solid productformed upon pouring onto ice water was collected byfiltration and recrystallized from ethanol-dimethylformamide to give (III-XX), respectively.

Reference： [1]Russian Journal of Bioorganic Chemistry,2016,vol. 42,p. 441 - 448

22
[ 144-83-2 ]
[ 69-72-7 ]
[ 599-79-1 ]

Yield	Reaction Conditions	Operation in experiment
95.4%		Example 4 Place sulfapyridine and 4 (amount of substance) hydrochloric acid (amount of substance of sulfapyridine is for 1) in a reaction flask. Stir until dissolve. Adjust temperature to 2C then start dropping 1.10sodium nitrite ( amount of substance of sulfapyridine is 1m).Allocate aqueous solution. React for 20min to obtain a solution containingdiazonium salt intermediate. Name this to be A. Place 1.3 salicylic acid and part of sodium hydroxide ( amount ofsubstance of sulfapyridine is 1m ) in a reaction flask. After adjustingtemperature to 7C,slowly start dropping the above-mentioned A to the above-mentioned reactionflask. At the same time, drop the remaining sodium hydroxide solution to controlthe pH of the reaction liquid to 10. Start reaction. The used amount of sodiumhydroxide is 4 (amount ofsubstance of sulfapyridine is 1m ). React for 1.5h. Stop reaction. Add THF tothe reaction mixture. Add hydrochloric acid to adjust pH to 3. Heat underreflux for a period of time. Cool to 30C to crystallize. Filter out crystals to obtain crudesulfasalazine. Place 10g crude sulfasalazine,70g dimethyl sulfoxide, 30g water in 250mL flask. Also, add solid sodiumhydroxide to mixture with pH of 9. Heat the mixture in the flask to 80oCto fully dissolve. After dissolving, add hydrochloric acid, dropwise, to adjustthe pH of the solution to 1. Incubate at 80Cfor 2h then cool to 0C then filter to obtain crude crystals. Add crystalsto water. Add solid sodium hydroxide. Heat to 80C. Dissolve to obtain solutionwith pH 9. Sequentially, undergo, at 70C, decolorization using 7g activatedcharcoal and filtration. Add, dropwise, hydrochloric acid to crystals with pH1.Dry crystals to obtain pure sulfasalazine. In this case, 9.54g ofpure sulfasalazineare collected. Yield is 95.4%. HLPC purity test shows 99.7%.
		A reaction flask was added with the above compound D, the mass of 4 hydrochloric acid (mass of sulfapyridine is 1), and stirred to dissolve. Temperature to 2 deg. C ,then was added dropwise by the mass of 1.10 sodium nitrite (mass of sulfapyridine is 1) aqueous solution, reacted for 20min, to obtain a solution containing a diazonium salt intermediate, A .The reaction flask was added 1.3 part of salicylic acid and a part of sodium hydroxide (to 1 part of sulfapyridine). At 7 deg. C was slowly added dropwise the above-mentioned A to the reaction flask, and the remaining sodium hydroxide solution was added dropwise to control the pH of the reaction solution to 10, then the reaction was started. 4 parts of sodium hydroxide (to 1 part of sulfapyridine). After the reaction for 1.5h, the reaction was stopped. THF was added to the reaction mixture, adding acid to adjust to pH 3, heated at reflux for a period of time. Then cooled to 30 deg. C to precipitate crystals. The crystals were filtered off, and the crystals were washed several times to give sulfasalazine. In this case the yield was 70.3%, by HLPC purity test was 98.6%.
		General procedure: Solution A (amine + HCl solution): 2,4-dimethylaniline (0.2918 g) was dissolved in approximately 0.8 mL of concentrated 32% HCl. DMF (20 mL) was added to this, after which the solution was made up to a volume (100 mL) with distilled water. Solution B (sodium nitrite solution): Sodium nitrite (0.2914 g) was dissolved in DMF (5 mL) and made up to a volume (50 mL) with distilled water. Solution C (coupler): 2-naphthol (0.35 g) was dissolved in 10% aqueous NaOH (10 mL) to which DMF (15 mL) was added. The pH of the solution was adjusted to 8.55-9 with 10% glycine solution. The solution was then made up to a volume (50 mL) with distilled water. Microreactor diazotization and consequent azo coupling reactions: A central composite experimental design with a total of 20 experimentswas used for this optimization study, where the diazotization of 2,4-dimethylaniline and its in situ azo coupling to 2-naphthol was used as a model reaction. The experiments were performed in a randomized manner. The temperature of the diazotization reaction was kept constant at 0 C while that of the azo coupling reaction was kept at 25 C (Table 10).

Reference： [1]Patent: CN105348184,2016,A .Location in patent: Paragraph 0049; 0050; 0051; 0052; 0053
[2]Patent: CN105330599,2016,A .Location in patent: Paragraph 0045; 0046
[3]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 1987 - 2004

23
[ 27914-73-4 ]
[ 144-83-2 ]
N-(sulfapyridine)-p-acetoxybenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With pyridine In acetone at 0 - 20℃; for 20h;
	With pyridine In acetone at 0 - 20℃; for 20h;	2.2. General Procedure for Sulfonamide Derivatives General procedure: Secondary sulfonamides were synthesized using naturally available 4-hydroxy and3,4,5-trihydroxy benzoic acids (gallic acid) in various plants and fruits, which were reacted with aceticanhydride to obtain 4-acetoxy and 3,4,5-triacetoxy benzoic acids for the protection of hydroxyl groups.Then, they were converted to their corresponding chloride derivatives by treating with thionyl chlorideto produce benzoyl chlorides, which underwent reactions with secondary sulfonamides having thiazole, pyrimidine, pyridine, isoxazole and thiadiazole groups to obtain secondary sulfonamidederivatives of acetoxybenzamides and triacetoxybenzamides as one part of target compounds.Deacetylation under acidic conditions gave the other part of our targeted sulfonamide derivatives [28].The reaction scheme is given in Figure 1.

Reference： [1]Gokcen, Taner; Gulcin, Ilhami; Ozturk, Turan; Goren, Ahmet C. [Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, vol. 31, p. 180 - 188]
[2]Köksal, Zeynep; Kalin, Ramazan; Camadan, Yasemin; Usanmaz, Hande; Almaz, Züleyha; Gülçin, Ilhami; Gokcen, Taner; Gören, Ahmet Ceyhan; Ozdemir, Hasan [Molecules, 2017, vol. 22, # 6]

24
[ 144-83-2 ]
[ 20665-85-4 ]
(E)-2-methoxy-4-(((4-(N-(pyridin-2-yl) sulfamoyl)phenyl)imino)methyl)phenyl isobutyrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In ethanol at 60 - 70℃;	2.3.1. Synthesis of Schiff base VA-sulfur drugs (3a-3r) General procedure: An equimolar mixture of VA derivative 1a-1f individually inlots of 1 mmole and substituted sulfanilamide 2a-2c in ethanolicsolution were stirred together and refluxed for 2-3h at60-70 C; thereafter, the reaction mixture was poured intoice-cold water and it was kept overnight in 15 C. Finally, theobtained precipitate was filtered and was dried at room temperatureand recrystallized with hot ethanol.

Reference： [1]Dehury, Budheswar; Padhy, Rabindra Nath; Paidesetty, Sudhir Kumar; Sahoo, Chita Ranjan; Sarathbabu, Subbarayan; Senthil Kumar, Nachimuthu [Journal of Biomolecular Structure and Dynamics, 2021]

25
[ 144-83-2 ]
[ 17028-61-4 ]
[ 2863537-23-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	In ethanol at 200℃; for 12h;	(E)-4-((2-hydroxy-3-methoxy-5-nitrobenzylidene)amino)-N-(pyridin-2-yl)benzenesulfonamide (1) To a solution of (0.997 g, 4 mmol) sulfapyridine dissolved in20mL absolute EtOH, (0.789 g, 4 mmol) 5-nitro-3-methoxy salicylaldehydedissolved in 15 mL absolute EtOH was addeddropwise. This reaction mixture has interacted at 200 C for12 h using the hydrothermal technique. The solid (powder)precipitate (Compound 1) were filtered, washed with coldEtOH and dried at room temperature. (428.41 g/mol). Yield:3.15 g (92%). M.p. 276 C. Anal. Calcd. for C19H16N4O6S: C,53.27; H, 3.76; N, 13.08; S, 7.48%. Found: C, 54.91; H, 3.95; N,13.37; S, 7.75.FTIR (ATR, tmax/cm1): 637, 757, 815, 910, 983, 1087, 1140(-SO2 sym), 1152, 1265, 1270 (C-O), 1327, 1331 (-SO2asym),1351 (N-O sym), 1531 (N-O asym), 1617 (CN), 1637(CN, aromatic), 2936 (C-H, methoxy str), 3125 (C-H, aromatic),3217 (N-H, sym), 3436 (O-H); 1H NMR (DMSO-d6, d,ppm): 14.24 (s, 1H, O-H), 11.52 (s, 1H, N-H), 9.20 (s, 1H,CHN), 8.33-6.56 (m, 10H, Ar-H), 4.00 (s, 3H, -OCH3); 13CNMR (DMSO-d6, d, ppm): 163.6 (C8), 160.6 (C7), 156.9 (C9),153.2 (C2), 152.8 (C13), 149.6 (C17),139.8 (C12), 139.2 (C4),138.5 (C15), 128.6 (C11), 122.1 (C10), 121.4 (C6), 117.2 (C5),116.1 (C16), 112.9 (C14), 110.7 (C3), 57.3 (C1).
92%	In ethanol at 200℃; for 12h;	(E)-4-((2-hydroxy-3-methoxy-5-nitrobenzylidene)amino)-N-(pyridin-2-yl)benzenesulfonamide (1) To a solution of (0.997 g, 4 mmol) sulfapyridine dissolved in20mL absolute EtOH, (0.789 g, 4 mmol) 5-nitro-3-methoxy salicylaldehydedissolved in 15 mL absolute EtOH was addeddropwise. This reaction mixture has interacted at 200 C for12 h using the hydrothermal technique. The solid (powder)precipitate (Compound 1) were filtered, washed with coldEtOH and dried at room temperature. (428.41 g/mol). Yield:3.15 g (92%). M.p. 276 C. Anal. Calcd. for C19H16N4O6S: C,53.27; H, 3.76; N, 13.08; S, 7.48%. Found: C, 54.91; H, 3.95; N,13.37; S, 7.75.FTIR (ATR, tmax/cm1): 637, 757, 815, 910, 983, 1087, 1140(-SO2 sym), 1152, 1265, 1270 (C-O), 1327, 1331 (-SO2asym),1351 (N-O sym), 1531 (N-O asym), 1617 (CN), 1637(CN, aromatic), 2936 (C-H, methoxy str), 3125 (C-H, aromatic),3217 (N-H, sym), 3436 (O-H); 1H NMR (DMSO-d6, d,ppm): 14.24 (s, 1H, O-H), 11.52 (s, 1H, N-H), 9.20 (s, 1H,CHN), 8.33-6.56 (m, 10H, Ar-H), 4.00 (s, 3H, -OCH3); 13CNMR (DMSO-d6, d, ppm): 163.6 (C8), 160.6 (C7), 156.9 (C9),153.2 (C2), 152.8 (C13), 149.6 (C17),139.8 (C12), 139.2 (C4),138.5 (C15), 128.6 (C11), 122.1 (C10), 121.4 (C6), 117.2 (C5),116.1 (C16), 112.9 (C14), 110.7 (C3), 57.3 (C1).
92%	With toluene-4-sulfonic acid In ethanol at 78℃; for 6h;	2.1. (E) -4-((2-hydroxy-3-methoxy-5-nitrobenzylidene)amino)-N- (pyridin-2-yl) benzenesulfonamide (1) To a solution of (1.99 g, 8 mmol) sulfapyridine dissolved in 20 mL absolute EtOH, (1.55 g, 8 mmol) 5-nitro-3-methoxy sali- cylaldehyde dissolved in 15 mL absolute EtOH was added drop- wise at 78 °C with continuous stirring for 6 h. In these reac- tions p -toluene sulfonic acid ( p -TsOH) was used as a catalyst. The precipitates (Compound 1) were filtered, washed with cold EtOH, and dried at room temperature. (428.41 g/mol) Yield: 3.15 g (92%). Anal. Calc. for C 19 H 16 N 4 O 6 S%: C 53.27; H 3.76; N 13.08; S 7.48%. Found,%: C 53.91; H 3.95; N 13.37; S 7.75. Compound 1 is very sol- uble in DMF, DMSO, EtOH, and MeOH. However, it is insoluble in water. FTIR (ATR, υmax /cm -1 ): 3436 υ(O -H str.), 3217 υs (N -H), 3125 υ(C -H, aromatic), 3030 υ(C -H, arom. str.), 2936 υ(C -H, methoxy str), 1637 υ(C = N, arom. str.), 1631 υ(C = C str.), 1617 υ(C = N), 1531 υas (N -O), 1474 υ(C -O, phenolic str.), 1331 υas (-SO 2 ), 1351 υs (N -O), 1327, 1270 υ(C -O str.), 1265, 1152, 1140 υs (-SO2), 1087, 983, 910, 815, 757, 637, 604, 586; 1 H NMR (DMSO-d 6 , δ, ppm): 14.24 s (OH), 11.53 s (N H ), 9.20 s (C H N), 8.10-6.55 m (ArH), 3.87 s (OC H 3 ); 13 C NMR (DMSO-d 6 , δ, ppm): 163.88 (C8), 160.57 (C7), 156.95 (C9), 153.27 (C2), 152.66 (C13), 149.65 (C17),139.72 (C12), 139.04 (C4), 138.33 (C15), 128.17 (C11), 122.00 (C10), 121.23 (C6), 117.22 (C5), 116.20(C16), 112.78 (C14), 110.28 (C3), 57.30 (C1); UV-vis (DMSO, λmax (nm) (log ): 250 (3.99), 258 (4.00), 278 (3.99), 390 (3.86), 478 (4.03). Fluorescence emission wavelength ( λem , nm) (2.00 ×10 -6 M in DMSO): 435

Reference： [1]Şahal, Hakan; Öz, Samet; Tekin, Suat; Canpolat, Erdal [Journal of Biomolecular Structure and Dynamics, 2023, vol. 41, # 10, p. 4361 - 4367]
[2]Şahal, Hakan; Öz, Samet; Tekin, Suat; Canpolat, Erdal [Journal of Biomolecular Structure and Dynamics, 2023, vol. 41, # 10, p. 4361 - 4367]
[3]Şahal, Hakan [Journal of Molecular Structure, 2023, vol. 1273]

26
[ 96-97-9 ]
[ 144-83-2 ]
[ 599-79-1 ]

Yield	Reaction Conditions	Operation in experiment
91 %	With potassium hydroxide In N,N-dimethyl-formamide Inert atmosphere; Reflux;	1-3 Example 1: 300g of DMF, 20g of potassium hydroxide, and 60g of sulfapyridine were added to a 500mL four-necked reaction flask, nitrogen was replaced three times, 44g of 4-nitrosalicylic acid was added under the protection of nitrogen, the temperature was raised to reflux reaction, TLC tracked until the reaction of sulfapyridine was complete , cool to normal temperature, filter, remove alkali, concentrate the filtrate under reduced pressure to half of the original volume, add dropwise 450mL of water under stirring, crystallize, filter to obtain crude sulfasalazine, and the crude product is purified by acid and alkali to obtain sulfasalazine Refined product 87.3g, total yield 91%, purity 99.1%.

Reference： [1]Current Patent Assignee: TIANHE PHARMACEUTICAL - CN115010660, 2022, A Location in patent: Paragraph 0021-0023

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A1256323[ 1228182-45-3 ]

Sulfapyridine-(phenyl-13C6)

Reason: Stable Isotope

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